반응 #2469282

반응 방정식

3-methyl-1H-pyrrolo[2,3-c]pyridine

KOtBu

DMF

BOC2O

→

3-methyl-pyrrolo[2,3-c]pyridin-1-yl amine

수율 35.0%

반응 조건

후처리

1. 1
   기타is purged with N2
2. 2
   workup.ADDITIONChloramine in ether (0.15 M, 92 mL) is added
3. 3
   workup.STIRRINGthe mixture is stirred for 20 min
4. 4
   온도The reaction is cooled to 00 C
5. 5
   workup.ADDITIONand a solution of Na2S2O3 (5 g) in water (80 mL) is added
6. 6
   workup.STIRRINGThe mixture is stirred for 10 min
7. 7
   농축concentrated in vacuo
8. 8
   기타The residue is triturated in DCM
9. 9
   여과filtered
10. 10
    workup.ADDITIONDCM is added
11. 11
    온도cooled to 0° C.
12. 12
    기타The resulting mixture is separated by silica gel chromatography
13. 13
    세척eluting with 10% MeOH in DCM

실험 절차

A mixture of 3-methyl-1H-pyrrolo[2,3-c]pyridine (1.21 g, 9.16 mmol), KOtBu (2.05 g, 18.3 mmol) in DMF (41 mL) is purged with N2 and stirred at rt for 2 h. Chloramine in ether (0.15 M, 92 mL) is added and the mixture is stirred for 20 min. The reaction is cooled to 00 C. and a solution of Na2S2O3 (5 g) in water (80 mL) is added. The mixture is stirred for 10 min, and then concentrated in vacuo. The residue is triturated in DCM and filtered. DCM is added, cooled to 0° C. and charged with BOC2O (541 mg, 2.48 mmol). The resulting mixture is separated by silica gel chromatography eluting with 10% MeOH in DCM to afford 3-methyl-pyrrolo[2,3-c]pyridin-1-yl amine (468 mg, 35%). MS: 148 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.85 (s, 1H), 8.27 (d, 1H), 7.46 (d, 1H), 7.09 (s, 1H), 2.30 (s, 3H).

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